
The Work Item - Real Talk on Tech's Toughest Career Choices
The web is full of podcasts that dole out generic career advice - “Follow your passion!”, “Keep learning!”, “Set clear goals!” This is all good if you're just starting out, but the pointers start to lose their luster quickly as you progress and start hitting invisible walls in your growth.
All of a sudden, it's harder to get promoted, opportunities to advance become more ambiguous, and the choices in front of you aren't as obvious as they were when you first started your job.
What does it take to get to the Staff engineer level? If you want to become an executive in the future, what should you do now to maximize your chances of hitting that goal? Should you have a time-bound career map or focus on unique opportunities that pop up serendipitously? Should you try your hand at entrepreneurship, and if so - how do you build a robust safety net?
For these questions and more, The Work Item is the podcast where I attempt to answer them with help from folks that went through trial by fire. They are not social media thought leaders - they are actual practitioners who have first-hand experience dealing with some of the more thorny challenges in this industry.
With folks like Jason Lengstorf (Founder, Learn With Jason), Craig Hewitt (Founder, Castos), Saron Yitbarek (Founder, CodeNewbie), Rob Walling (Founder, MicroConf), Cedric Chin (Founder, CommonCog), Jason Fried (CEO, 37signals), Gennadiy Korol (CEO, Moon Studios), Mayuko Inoue (iOS Engineer, Apple), Camille Fournier, and many, many more you will get extraordinary insights that will help you unlock your career potential beyond the basics you'll learn elsewhere.
Latest episodes

Mar 11, 2022 • 41min
#51 - Finding Your Engineering Passion, with Vicente Plata of 500 Startups LatAm, Shopify, and More
Vicente Plata is doing way more than one would expect from an engineering leader - not only is he an engineering manager, but he also advises startups and communities, is deeply involved in various mentorship programs, and is someone who is always eager to help.
In this episode we sit down to chat more about his aspirations, how he balances time between all the responsibilities, and what someone working in tech can do to accelerate their career on an exponential trajectory.
You can find Vicente on the following sites:
🐤 Twitter📝 Website
The podcast was produced by Den Delimarsky. Music by Wataboi from Pixabay.
Feedback
If you haven't already, make sure to subscribe to the show and leave a review or a rating, wherever you are getting your podcast. I really appreciate your feedback and am working to make this podcast more useful for you, the listener, with every episode. Ratings and feedback make it so others can easily discover and enjoy the insights you listen to here!

Mar 4, 2022 • 41min
#50 - Problem And Product Management, with Isaac Hepworth
Today I chat with a good friend, mentor, and an all-around great person - Isaac Hepworth. Isaac is the person you should go to if you want to learn more about what it means to be achieving excellence in the product management space. We chat about the role of a problem solver, what it means to be a PM across different companies and titles, and what one can do to better prepare for an industry that changes by the day.
You can find Isaac on the following sites:
🐤 Twitter
The podcast was produced by Den Delimarsky. Music by Wataboi from Pixabay.
Feedback
If you haven't already, make sure to subscribe to the show and leave a review or a rating, wherever you are getting your podcast. I really appreciate your feedback and am working to make this podcast more useful for you, the listener, with every episode. Ratings and feedback make it so others can easily discover and enjoy the insights you listen to here!

Feb 17, 2022 • 37min
#49 - Product Management in Government, with Director of Product Management for the City and County of San Francisco, Adrianna Tan
Despite starting a career in product management at one of the big companies, I've never considered to do the same job but working for the government. Not because I didn't want to. Mainly, because I did not know that was even an option. As it turns out - it is, in fact, an option, and a pretty impactful one at that.
To learn more about this career trajectory, I chatted with Adrianna Tan, Director of Product Management for the City and County of San Francisco. She shares her journey as a founder of startups and non-profits, an avid hiker and an advocate for an open web, and how it all combines in her work.
You can find Adrianna on the following sites:
🐤 Twitter
📝 Blog
The podcast was produced by Den Delimarsky. Music by Wataboi from Pixabay.
Feedback
If you haven't already, make sure to subscribe to the show and leave a review or a rating, wherever you are getting your podcast. I really appreciate your feedback and am working to make this podcast more useful for you, the listener, with every episode. Ratings and feedback make it so others can easily discover and enjoy the insights you listen to here!

Feb 6, 2022 • 38min
#48 - The Story of Working In Developer Relations, with Dan Shaw
This is the brand-new start of the third season of The Work Item podcast, and to make the kick-off even better I sat down with our good friend of the show, Dan Shaw, to learn more about their career. Dan shares the story of bootstrapping a Developer Relations arm at PayPal, wisdom around career decisions, and much more in this episode.
You can find Dan on the following sites:
🐤 Twitter
📝 Blog
The podcast was produced by Den Delimarsky. Music by Wataboi from Pixabay.
Feedback
If you haven't already, make sure to subscribe to the show and leave a review or a rating, wherever you are getting your podcast. I really appreciate your feedback and am working to make this podcast more useful for you, the listener, with every episode. Ratings and feedback make it so others can easily discover and enjoy the insights you listen to here!

Dec 12, 2021 • 60min
#47 - 2021 Reflections, Creativity, and More, with Mayuko Inoue
The end of 2021 is almost here, and it's time to wrap up the second season of The Work Item. And what better way to do that than to invite a good friend on the show to talk about their journey through the past 12 months? In this episode, I am chatting with Mayuko Inoue about all things 2021, the best choices in comfort foods, McDonalds french fries, thoughts on the content creator career path, and more.
We wanted to make this episode very informal, yet informative. To borrow Mayuko's intro to her own podcast, Muko's Corner (which you should subscribe to) - sit down, get cozy, grab a cup of tea, and enjoy the show!
You can find Mayuko on the following sites:
🎥 YouTube🐤 Twitter📸 Instagram📝 Blog🦹♀️ Twitch🎙 Podcast (Muko's Corner)
If you haven't yet seen Mayuko's “A Day In The Life of a Software Engineer” and “Why Japan Fell Behind in the Tech Industry” - add them to your watch queue!
As a side-note, you can also check out my interview with Mayuko on her channel.
The podcast was produced by Den Delimarsky. Music by Wataboi from Pixabay.
Feedback
If you haven't already, make sure to subscribe to the show and leave a review or a rating, wherever you are getting your podcast. I really appreciate your feedback and am working to make this podcast more useful for you, the listener, with every episode. Ratings and feedback make it so others can easily discover and enjoy the insights you listen to here!

Dec 5, 2021 • 58min
#46 - From Journalism to Developer Engagement, with Christina Warren
The myth of the superhero programmer - we often hear about it, but it's rarely the reality. Being a superhero on a team takes more than just technical chops, and that's one of the topics that I chat about today with Senior Developer Advocate at Microsoft - Christina Warren. You might've seen Christina before on This Week on Channel 9, or even back in the day - at Gizmodo and Mashable.
This episode ended up being less of a career chat and more of a friendly exchange about the latest happenings and what we can learn from them. Yes, we even talk a bit about the re-released Grand Theft Auto: The Definitive Edition.
You can find Christina on the following sites:
🐤 Twitter📝 Website📷 Instagram
And if you want to see more of Clippy (the beloved Office assistant) come to life, you absolutely have to help Christina get to 10,000 followers on Instagram.
The podcast was produced by Den Delimarsky. Music by Wataboi from Pixabay.
Feedback
If you haven't already, make sure to subscribe to the show and leave a review or a rating, wherever you are getting your podcast. I really appreciate your feedback and am working to make this podcast more useful for you, the listener, with every episode. Ratings and feedback make it so others can easily discover and enjoy the insights you listen to here!

Nov 28, 2021 • 54min
#45 - Startups, Growth, and A Quest to Build People-focused Companies, with Jennifer Kim
The decision to join a startup or a big company is not an easy one, as one has to consider many factors that go beyond just the financial side of things. In this episode, I talk to Jennifer Kim, a seasoned startup advisor with a lot of experience dealing with these kinds of decisions and more. Jennifer also specializes in the people part of the startup equation - arguably, one of the hardest ones. We chat about the current challenges startups encounter in this space, why it's important to build a diverse workforce, and what one individual can do to be a changemaker in their company's culture.
You can find Jennifer on the following sites:
🐤 Twitter📝 Website
The podcast was produced by Den Delimarsky. Music by Wataboi from Pixabay.
Feedback
If you haven't already, make sure to subscribe to the show and leave a review or a rating, wherever you are getting your podcast. I really appreciate your feedback and am working to make this podcast more useful for you, the listener, with every episode. Ratings and feedback make it so others can easily discover and enjoy the insights you listen to here!

Nov 14, 2021 • 1h 1min
#44 - So What Is Product Marketing, with Isaac Levin
You've probably heard of the many types of PM - project managers, product managers, and even program managers. But did you also know that there is a PMM - product marketing manager? I wasn't quite sure what the responsibilities of one would be, so I reached out to Isaac Levin - Principal Product Marketing Manager at Elastic, and asked him to talk about his work.
You can find Isaac on the following sites:
🐤 Twitter📝 Blog🐱 GitHub📹 Twitch
Make sure to also check out Isaac's podcast - Coffee and Open Source.
The podcast was produced by Den Delimarsky. Music by Wataboi from Pixabay.
Feedback
If you haven't already, make sure to subscribe to the show and leave a review or a rating, wherever you are getting your podcast. I really appreciate your feedback and am working to make this podcast more useful for you, the listener, with every episode. Ratings and feedback make it so others can easily discover and enjoy the insights you listen to here!

Nov 7, 2021 • 58min
#43 - Ins And Outs Of Developer Advocacy, with Brian Douglas
Developer Advocacy is a relatively new field, but when it comes to knowing how to navigate it, Brian Douglas' knowledge is second to none. As Director of Developer Advocacy at GitHub, he is at the forefront of a lot of the developer engagement efforts - from understanding the pain points of those that use GitHub, to advocating for new initiatives and programs.
I sit down with Brian to learn more about what it takes to be a great developer advocate, how one can break into the field, and how you measure success in the role. Suffice to say - it was a packed conversation and we needed more time and maybe even a future follow-up to cover everything.
You can find Brian on the following sites:
🐤 Twitter📝 Blog🐱 GitHub📹 Twitch📧 Newsletter
Also, check out This Developing Story and Jamstack Radio - both podcasts that Brian runs!
The podcast was produced by Den Delimarsky. Music by Wataboi from Pixabay.
Feedback
If you haven't already, make sure to subscribe to the show and leave a review or a rating, wherever you are getting your podcast. I really appreciate your feedback and am working to make this podcast more useful for you, the listener, with every episode. Ratings and feedback make it so others can easily discover and enjoy the insights you listen to here!

Oct 31, 2021 • 59min
#42 - Building The World You Want To See, with Jeff Atwood
Whether you are new in the tech industry or are a veteran developer, chances are that you've used a product that Jeff Atwood worked on. I'm talking about Stack Overflow and Discourse, of course. When it comes to building communities and fostering good conversations, Jeff took an unusual position - steer the conversation towards finding the best in people, argue ideas and not people, and ultimately, contribute to a world that's just a bit better. How does it all work? Jeff elaborates in this episode.
You can find Jeff on the following sites:
🐤 Twitter
📝 Blog
As called-out on the show, you should check out Discourse, along with the Meta and Boing Boing communities.
The podcast was produced by Den Delimarsky. Music by Wataboi from Pixabay.
Feedback
If you haven't already, make sure to subscribe to the show and leave a review or a rating, wherever you are getting your podcast. I really appreciate your feedback and am working to make this podcast more useful for you, the listener, with every episode. Ratings and feedback make it so others can easily discover and enjoy the insights you listen to here!